Ethanol → (-)-4-{[1-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethyloxy]carbonyl}benzoic acid

HRID 1756464Notes

Reaction equation

HRID 1756464 reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]([O:16][C:17]([C:19]3[CH:30]=[CH:29][C:22]([C:23]([O:25]CC=C)=[O:24])=[CH:21][CH:20]=3)=[O:18])[CH3:15])[CH:5]=[CH:4][C:3]1=2.N1CCOCC1.C(O)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:31][C:2]1([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:14]([O:16][C:17]([C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:29][CH:30]=3)=[O:18])[CH3:15])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 3

HCID 702EthanolHCID 8083MorpholineHCID 21474484Allyl 4-{[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethyloxy]carbonyl}benzoate

Product 1

HCID 21474501(-)-4-{[1-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethyloxy]carbonyl}benzoic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.40 g (5.71 mmol) of the ester obtained in Example 59 (b) in 30 ml of THF is treated with mg of tetrakis(triphenylphosphine)palladium(0) and 5 ml of morpholine under the preparation conditions of Example 24(b), to yield 1.94 g (89%) of the expected derivative, melting point 138° C. (αD =-53.2°; c=1, ethanol).

Sources & evidence

ORD record
ord-f19256d5c67f409487c22fdad229c852
Source dataset
uspto-grants-1995_08
Patent number
US05439925

Reaction notes

Loading…